(The Root) -- Amazing Fact About the Negro No. 32: Were there any successful slavery escapes by sea?

Two weeks ago, we saw how Henry Box Brown mailed himself to freedom by carriage, steamer and train. This week, we meet a man who took a more direct route through the very waters where the Civil War began, Charleston Harbor, S.C., from which, incredibly, he sailed himself, his family and the fellow slave members of his crew to freedom.

Just before dawn on May 13, 1862, Robert Smalls and a crew composed of fellow slaves, in the absence of the white captain and his two mates, slipped a cotton steamer off the dock, picked up family members at a rendezvous point, then slowly navigated their way through the harbor. Smalls, doubling as the captain, even donning the captain's wide-brimmed straw hat to help to hide his face, responded with the proper coded signals at two Confederate checkpoints, including at Fort Sumter itself, and other defense positions. Cleared, Smalls sailed into the open seas. Once outside of Confederate waters, he had his crew raise a white flag and surrendered his ship to the blockading Union fleet.

In fewer than four hours, Robert Smalls had done something unimaginable: In the midst of the Civil War, this black male slave had commandeered a heavily armed Confederate ship and delivered its 17 black passengers (nine men, five women and three children) from slavery to freedom.

Sailing From Slavery to Freedom

Our story begins in the second full year of the war. It is May 12, 1862, and the Union Navy has set up a blockade around much of the Atlantic and Gulf Coasts. Inside it, the Confederates are dug in defending Charleston, S.C., and its coastal waters, dense with island forts, including Sumter, where the first shots of the Civil War were fired exactly one year, one month, before. Attached to Brig. Gen. Roswell Ripley's command is the C.S.S. Planter, a "first-class coastwise steamer" hewn locally for the cotton trade out of "live oak and red cedar," according to testimony given in a U.S. House Naval Affairs Committee report 20 years later.

Pictured: Robert Smalls (Library of Congress, c. 1870).

After two weeks of supplying various island points, the Planter returns to the Charleston docks by nightfall. It is due to go out again the next morning and so is heavily armed, including approximately 200 rounds of ammunition, a 32-pound pivot gun, a 24-pound howitzer and four other guns, among them one that had been dented in the original attack on Sumter. In between drop-offs, the three white officers on board (Capt. C.J. Relyea, pilot Samuel H. Smith and engineer Zerich Pitcher) make the fateful decision to disembark for the night -- either for a party or to visit family -- leaving the crew's eight slave members behind. If caught, Capt. Relyea could face court-martial -- that's how much he trusts them.

At the top of the list is Robert Smalls, a 22-year-old mulatto slave who's been sailing these waters since he was a teenager: intelligent and resourceful, defiant with compassion, an expert navigator with a family yearning to be free. According to the 1883 Naval Committee report, Smalls serves as the ship's "virtual pilot,"but because only whites can rank, he is slotted as "wheelman." Smalls not only acts the part; he looks it, as well. He is often teased about his resemblance to Capt. Relyea: Is it his skin, his frame or both? The true joke, though, is Smalls' to spring, for what none of the officers know is that he has been planning for this moment for weeks and is willing to use every weapon on board to see it through.

Background

Smalls was born on April 5, 1839, behind his owner's city house at 511 Prince Street in Beaufort, S.C. His mother, Lydia, served in the house but grew up in the fields, where, at the age of nine, she was taken from her own family on the Sea Islands. It is not clear who Smalls' father was. Some say it was his owner, John McKee; others, his son Henry; still others, the plantation manager, Patrick Smalls. What is clear is that the McKee family favored Robert Smalls over the other slave children, so much so that his mother worried he would reach manhood without grasping the horrors of the institution into which he was born. To educate him, she arranged for him to be sent into the fields to work and watch slaves at "the whipping post."

"The result of this lesson led Robert to defiance," wrote great-granddaughter Helen Boulware Moore and historian W. Marvin Dulaney, and he "frequently found himself in the Beaufort jail." If anything, Smalls' mother's plan had worked too well, so that "fear[ing] for her son's safety … she asked McKee to allow Smalls to go to Charleston to be rented out to work." Again her wish was granted. By the time Smalls turned 19, he had tried his hand at a number of city jobs and was allowed to keep one dollar of his wages a week (his owner took the rest). Far more valuable was the education he received on the water; few knew Charleston harbor better than Robert Smalls.

It's where he earned his job on the Planter. It's also where he met his wife, Hannah, a slave of the Kingman family working at a Charleston hotel. With their owners' permission, the two moved into an apartment together and had two children: Elizabeth and Robert Jr. Well aware this was no guarantee of a permanent union, Smalls asked his wife's owner if he could purchase his family outright; they agreed but at a steep price: $800. Smalls only had $100. "How long would it take [him] to save up another $700?" Moore and Dulaney ask. Unwittingly, Smalls' "look-enough-alike," Captain Rylea, gave him his best backup.

To white Confederates, the Union ships blocking their harbors were another example of the North's enslavement of the South; to actual slaves like Robert Smalls, these ships signaled the tantalizing promise of freedom. Under orders from Secretary Gideon Welles in Washington, Navy commanders had been accepting runaways as contraband since the previous September. While Smalls couldn't afford to buy his family on shore, he knew he could win their freedom by sea -- and so he told his wife to be ready for whenever opportunity dawned.

The Escape on the Planter

That opportunity is at hand on the night of May 12. Once the white officers are on shore, Smalls confides his plan to the other slaves on board. According to the Naval Committee report, two choose to stay behind. "The design was hazardous in the extreme," it states, and Smalls and his men have no intention of being taken alive; either they will escape or use whatever guns and ammunition they have to fight and, if necessary, sink their ship. "Failure and detection would have been certain death," the Navy report makes plain. "Fearful was the venture, but it was made."

At 2:00 a.m. on May 13, Smalls dons Capt. Rylea's straw hat and orders the Planter's skeleton crew to put up the boiler and hoist the South Carolina and Confederate flags as decoys. Easing out of the dock, in view of Gen. Ripley's headquarters, they pause at the West Atlantic Wharf to pick up Smalls' wife and children, along with four other women, three men and another child.

At 3:25 a.m., the Planter accelerates "her perilous adventure," the Navy report continues (it reads more like a Robert Louis Stevenson novel). From the pilot house, Smalls blows the ship's whistle while passing Confederate Forts Johnson and, at 4:15 a.m., Fort Sumter, "as cooly as if General Ripley was on board." Smalls not only knows all the right Navy signals to flash; he even folds his arms like Capt. Rylea, so that in the shadows of dawn, he passes convincingly for white.

"She was supposed to be the guard boat and allowed to pass without interruption," Confederate Aide-de-Campe F.G. Ravenel explains defensively in a letter to his commander hours later. It is only when the Planter passes out of Rebel gun range that the alarm is sounded -- the Planter is heading for the Union blockade. Approaching it, Smalls orders his crew to replace the Palmetto and Rebel flags with a white bed sheet his wife brought on board. Not seeing it, Acting Volunteer Lt. J. Frederick Nickels of the U.S.S. Onward orders his sailors to "open her ports." It is "sunrise," Nickels writes in a letter the same day, an illuminating fact that may have changed the course of history, at least on board the Planter -- for now Nickels could see.

In The Negro's Civil War, the dean of Civil War studies James McPherson quotes the following eyewitness account: "Just as No. 3 port gun was being elevated, someone cried out, 'I see something that looks like a white flag'; and true enough there was something flying on the steamer that would have been white by application of soap and water. As she neared us, we looked in vain for the face of a white man. When they discovered that we would not fire on them, there was a rush of contrabands out on her deck, some dancing, some singing, whistling, jumping; and others stood looking towards Fort Sumter, and muttering all sorts of maledictions against it, and 'de heart of de Souf,' generally. As the steamer came near, and under the stern of the Onward, one of the Colored men stepped forward, and taking off his hat, shouted, 'Good morning, sir! I've brought you some of the old United States guns, sir!' " That man is Robert Smalls, and he and his family and the entire slave crew of the Planter are now free.

After "board[ing] her, haul[ing] down the flag of truce, and hoist[ing] the American ensign" (his words), Lt. Nickels transfers the Planter to his commander, Capt. E.G. Parrott of the U.S.S. Augusta. Parrott then forwards it on to Flag Officer Samuel Francis Du Pont (of the "du Pont" Du Ponts), at Port Royal, Hilton Heads Island, with a letter describing Smalls as "very intelligent contraband." Du Pont is similarly impressed, and the next day writes a letter to the Navy secretary in Washington, stating, "Robert, the intelligent slave and pilot of the boat, who performed this bold feet so skillfully, informed me of [the capture of the Sumter gun], presuming it would be a matter of interest." He "is superior to any who have come into our lines -- intelligent as many of them have been." While Du Pont sends the families to Beaufort, he takes care of the Planter's crew personally while having its captured flags mailed to Washington via the Adams Express, the same private carrier that had delivered Box Brown to freedom in 1849.

The Reception

Smalls may not have had the $700 he needed to purchase his family's freedom before the war; now, because of his bravery and his inability to purchase his wife, the U.S. Congress on May 30, 1862, passed a private bill authorizing the Navy to appraise the Planter and award Smalls and his crew half the proceeds for "rescuing her from the enemies of the Government." Smalls received $1,500 personally, enough to purchase his former owner's house in Beaufort off the tax rolls following the war, though according to the later Naval Affairs Committee report, his pay should have been substantially higher.

The Confederates seemed to know this already; after Smalls' escape, biographer Andrew Billingsley notes, they put a $4,000 bounty on his head. Still, those on the scene had a hard time explaining how slaves pulled off such a feat; in the aftermath, Aide-de-Campe Ravenel even intimated to his commander that the night before, "it would appear that … two white men and a white woman went on board of her, and as they were not seen to return it is supposed that they have also gone with her." Suppose all they wanted -- there was no record of any white passengers aboard the Planter the morning of May 13 -- Smalls and his crew had acted alone. As his contemporary steamer pilot Mark Twain famously wrote: "Facts are stubborn things."

In the North, Smalls was feted as a hero and personally lobbied the Secretary of War Edwin Stanton to begin enlisting black soldiers. After President Lincoln acted a few months later, Smalls was said to have recruited 5,000 soldiers by himself. In October 1862, he returned to the Planter as pilot as part of Admiral Du Pont's South Atlantic Blockading Squadron. According to the 1883 Naval Affairs Committee report, Smalls was engaged in approximately 17 military actions, including the April 7, 1863, assault on Fort Sumter and the attack at Folly Island Creek, S.C., two months later, where he assumed command of the Planter when, under "very hot fire," its white captain became so "demoralized" he hid in the "coal-bunker." For his valiancy, Smalls was promoted to the rank of captain himself, and from December 1863 on, earned $150 a month, making him one of the highest paid black soldiers of the war. Poetically, when the war ended in April 1865, Smalls was on board the Planter in a ceremony in Charleston Harbor.

Robert Smalls' Postwar Record

Following the war, Smalls continued to push the boundaries of freedom as a first-generation black politician, serving in the South Carolina state assembly and senate, and for five nonconsecutive terms in the U.S House of Representatives (1874-1886) before watching his state roll back Reconstruction in a revised 1895 constitution that stripped blacks of their voting rights. He died in Beaufort on February 22, 1915, in the same house behind which he had been born a slave and is buried behind a bust at the Tabernacle Baptist Church. In the face of the rise of Jim Crow, Smalls stood firm as an unyielding advocate for the political rights of African Americans: "My race needs no special defense for the past history of them and this country. It proves them to be equal of any people anywhere. All they need is an equal chance in the battle of life."

Henry Louis Gates Jr. is the Alphonse Fletcher University Professor and the director of the W.E.B. Du Bois Institute for African and African-American Research at Harvard University. He is also the editor-in-chief of The Root. Follow him on Twitter and Facebook.